


Cat boy Tommy

by Merciignoremoi



Category: Video Blogging RPF
Genre: Boys in Skirts, Butt Plugs, Dubious Consent, Guilt, Lovesickness, M/M, Webcam/Video Chat Sex, kitten play
Language: English
Status: Completed
Published: 2021-01-08
Updated: 2021-01-09
Packaged: 2021-03-12 06:35:28
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, Underage
Chapters: 2
Words: 1,833
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28631109
Author URL: https://archiveofourown.org/users/Merciignoremoi/pseuds/Merciignoremoi
Summary: Tommy loses a bet and meets a sub goal.
Relationships: Wilbur Soot/TommyInnit
Comments: 13
Kudos: 333





	1. Streaming

Tommy was very reluctant to do this stream. He had made a bet, and set a sub goal along with it.

He met the goal and lost the bet.

The bet was that if Wilbur beat him in bed wars, he would wear a skirt. He lost that bet very quickly. He then set a sub goal, he would wear cat ears and a tail if he reached it. And he reached it in the same hour he had set it.

They agreed wilbur would pick the skirt and they would contact a friend of Wilbur’s to make the ears & tail.

He had grabbed the packages off of the front dooor step before his mom noticed. He was slightly embarrassed about the outfit. Not about the skirt, oh no, he was okay with that. It was the cat elements.

When he had opened the box he was greeted with a soft black shirt, pretty normal, but it looked like it might be a bit short on him. He didn’t really mind, he was gonna wear boxers under it.

The problem came when he opened the second package. The ears were fine, they matched his hair to a T. But the tail.

He didn’t think he had told his friend Tommy was a minor. Why does he say that you ask? Oh, he doesn’t know, maybe because this friend had sent Tommy a tail butt plug?

He wasn’t gonna back out now though. So he did what any rational person would do. He didn’t tell anyone it was a butt plug. He took a pair of boxers he didn’t care about, and cut a hole in the back for the tail. He would just say he clipped it to his boxers to make it look better. Yeah, that was convincing.

All he needed to do now was to try and get the plug in his ass.

———Line break———

On Friday, the day of the scheduled stream, he would say he was pretty used to the plug.

Hell, he had fallen asleep with it in last night. Needless to say, it was odd to wake up half naked, wth a butt plug up his ass. He didn’t bother to get dressed just yet, his mother having brought his breakfast up to him like she did on the weekends.

He logged onto his discord, messaging Wilbur to see if they were still doing the stream. Wilbur said the were, so Tommy ate his breakfast, and got dressed at his own pace.

He pulled on the boxers he had modified. He had tried on the full outfit on Thursday. The skirt was a bit short, but it was nice. He had made a mental note to buy himself a few more skirts.

Putting on the cat ears and final touches, he sat down at his desk. He rung Wilbur up, not putting his camera on just yet.

“Hey, Tommy. Did you chicken out?” Wilbur teased, cocking an eyebrow.

“No! I just wanted to do a dramatic reveal.” Tommy huffed, flicking on his cam. He stepped back from his desk, revealing the full outfit. He slowly turned around to show the full outfit. The tail swished between his legs, moving the skirt as well.

Wilbur sat there in shock. “Tommy...where is that tail attached?” The older man said, his voice shaking.

“It’s clipped to my boxers. Thought it looked better.” Tommy shrugged, lieing through his teeth. He would tell Wilbur after the stream.

Wilbur let out the breath he had been holding. He clicked to start stream button at the same time Tommy did.

The chat was going wild. They hadn’t thought Tommy would do it. Things like ‘cat boy Tommy’ and ‘pretty kitty’ filled the chat. Tommy was enjoying all the praise and compliments.

“I see you like my outfit chat! I do too. I ordered some more skirts. I think I like them. Spinning is fun. Not gonna spin in this one though. It’s a bit short.” Tommy joked. He sat down at his desk to answer some questions and talk with chat.

Wilbur and Tommy spent about an hour talking to chat and laughing. They sang one of Wilbur’s songs together; The internet ruined me, Tommy’s favorite of Wilbur’s songs.

“Okay chat, I’m hungry. So I’m gonna sign off for now. Might hop back on later.” Tommy said, ending the stream.

Tommy turned off his face cam in the call. “Hey, Wilbur, are you done with your stream? I wanna show you something.” Tommy asked.

“Yeah, let me just end it real quick and then put my guitar away.” Wilbur said, clicking a few buttons.  
This was it. Now all he had to do was wait.


	2. I want to show you something

While Wilbur ended his stream Tommy stood up and took off his boxers, leaving the skirt on.

He waited patiently, shifting in his seat. He turned his camera back on.

“Okay, Tommy. What is it you wanted to show me?” Wilbur asked, leaning back in his chair.

Tommy took a deep breath and got up from his desk. 

“You know how I said the tail was clipped to my boxers?”, Wilbur nodded nervously, “That was a lie.” He said, biting his lip.

“What? Where else could it be attached? I told her to send you a clip on tail.” Wilbur asked. That was, unless she had acted of her own accord. She was the only one who knew about his feelings for the young boy.

Tommy didn’t answer him, instead, he turned around and bent over.

He whole ass was on display for the older man. He reached behind himself to pull his cheeks apart, showing just how the blonde tail was attached.

Wilbur let out a choked noise, eyes going wide. The tail was a plug. It looked big too.

“Do you like it? I mean, you were the one to send it to me.” Tommy said, peaking over his shoulder.

Wilbur was in disbelief. The boy he had been lusting after for months was bending over and spreading his cheeks for him. He could get in so much trouble for this. But, Wilbur never one to look a gift horse in the mouth, took the bait.

“I do, kitty. You look so cute.” Wilbur said, eating up the image on his screen.

Tommy went beat red. “Wilbur! I didn’t expect you to really take the bait!” Tommy yelled, whipping back around to face the camera.

That sentence worried Wilbur. “What do you mean bait?” He asked in a stern tone.

“I mean I didn’t expect you to call me kitty! Or flirt back! I was just supposed to make you flustered! Not the other way around!” Tommy shouted, the flush on his face reaching his ears.

“Well, to be fair, you just showed me your ass.” Wilbur snarked back, glaring playfully at the boy. That’s when he noticed it.

“Wait. Is that my hoodie that you borrowed when we met up with fundy and niki cuz you forgot yours?” Wilbur asked leaning forward to get a better look.

“So what if it is?” Tommy retorted. “And guess what? I slept with the plug in last night too. Didn’t even realize it.” He said, smirking.

Wilbur sputtered, he didn’t want Tommy’s words to be hot. He really didn’t, he promises! But the way   
Tommy looked at him though the camera, it was so attractive. Wilbur wimpered, eyes closing slightly and thighs pressing together.

“Does that turn you on? Knowing I slept in only in your sweater with a plug up my ass?” The boy teased, wiggling in his chair. He was having fun with this, seeing Wilbur all needy.

“Is it like I’m your kitty? Your little fucktoy? Wanna stuff your dick in me?” Tommy taunted turning around and standing once more. He slipped off the skirt, kneeling on his bed, ass in the air, still facing the camera. He swayed his hips as best he could in this position.

“Do you like that, Wilby? Am I being a good kitty? Shaking my ass for you. My door isn’t even locked, my family could walk in at any moment! And what would they think when they saw you, a grown man getting off to a teenager with a butt plug up his ass. A plug that you sent him no no less!” Tommy said, a smile on his face.

This is just what he wanted. No more sleepless nights wanking to Wilbur’s image in his head, he had the real thing right in his grasp!

“T-Tommy...you really need to stop...I don’t...” Wilbur pleaded, panting hard. He was really trying, he was but it was too much, he needed to touch himself. He popped the button on his jeans and slid the zipper down, shimming out of his pants as fast as he could.

Tommy felt sick, his throat burning, chest lighting on fire. He wasn’t disgusted, oh no, he was love sick. Wilbur was so hot to him. He let out a sickly little giggle, focus solely on his Wilbur.

“Wanna see something I got myself? I got it when the plug wasn’t enough.” Tommy said. Reaching into his night stand, he pulled out a large flesh colored dildo and a big bottle of lube.

“Do you like it? I got it with you in mind. Don’t think I can’t see how huge you are.” Tommy asked, licking a stripe up the dildo.

Wilbur was shocked, how had he gotten it right? The toy was the exact same size as his cock, if not a little thicker.

“Tommy... stop...” He protested weakly, not stopping the hand on his dick, imagining it was Tommy jerking him off instead. He watched as Tommy slicked the dildo up, pressing it against his hole.

“Fuck! God, Wilbur I wish you were here. Want you so bad, want your cock.” The blonde all but moaned, eyes rolling back in his head as the toy was pressed into the hilt. He wasted no time starting a brutal pase for himself, fucking himself on the fake cock.

“Fuck, Wilbur...you feel so good! Fuck me harder, faster!” Tommy moaned. He was fucking himself so fast his hand was a blur as he used the toy to pleasure himself. His eyes rolled back into his head as he came, cum splattering all over the sweater that he still wore.

Wilbur came at the sight of the beautiful blonde boy on his knees, fake cock pounding into his ass. He came with a shout, the young boy’s name on his lips.

——Line break——

He came to about ten minutes later, Tommy having ended the call.

The post-nut clarity was strong, guilt coming in waves. He shouldn’t have done that. He violated Tommy’s privacy. As soon as the boy had showed him his ass he should have hung up.

But it was too late now, what’s done is done. He would tell all his friends and turn himself over to the cops in the morning.

**Notes for the Chapter:**

> Thank you for reading! I DO NOT support hate of any kind on my own or others works. Keep that shit to yourself.

**Author's Note:**

> Thank you for reading! This is a tumblr commission. I do not support pedophilia. Next chapter up later today or early tomorrow morning.


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